Synthesis and conformational analysis of poly(phenylacetylene)s with serinol-tethered carbohydrate appendages

We synthesized phenylacetylenes containing β-lactoside, β-cellobioside, or β-maltoside, and polymerized them to produce the corresponding poly (phenylacetylene)s. In these poly (phenylacetylene)s, the pendent carbohydrates were tethered to the mainchains by serinol spacers. Because similar glycosyl...

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Bibliographic Details
Published in:	Carbohydrate research Vol. 481; pp. 23 - 30
Main Authors:	Masubuchi, Kana, Maehata, Masakiyo, Suzuki, Chieko, Matsuoka, Ryoji, Sekiguchi, Maki, Chigira, Naoto, Amano, Yoshitsugu, Inokuchi, Mayu, Li, Qintong, Hasegawa, Teruaki
Format:	Journal Article
Language:	English
Published:	Netherlands Elsevier Ltd 15-07-2019
Subjects:	Acetylene - analogs & derivatives Acetylene - chemical synthesis Acetylene - chemistry Carbohydrate–carbohydrate interaction Chemistry Techniques, Synthetic Glycocluster Glycosylation Helical structure Helix–coil transition Molecular Conformation Molecular Dynamics Simulation poly(phenylacetylene) Polymerization Propanolamines - chemistry Propylene Glycols - chemistry Salts - chemistry Spatial carbohydrate packing Stereoisomerism Sugars - chemistry Water - chemistry Glycocluster Carbohydrate–carbohydrate interaction Spatial carbohydrate packing poly(phenylacetylene) Helical structure Helix–coil transition
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Summary:	We synthesized phenylacetylenes containing β-lactoside, β-cellobioside, or β-maltoside, and polymerized them to produce the corresponding poly (phenylacetylene)s. In these poly (phenylacetylene)s, the pendent carbohydrates were tethered to the mainchains by serinol spacers. Because similar glycosyl serinol units are found in the natural glycosphingolipids in cell membranes, the densely packed carbohydrate clusters along the poly (phenylacetylene) mainchains act as molecular mimics of cell surface glycoclusters. We analyzed the conformation of the glycosylated poly (phenylacetylene)s using circular dichroism spectroscopy, and found that the spatial carbohydrate packing within the glycoclusters changed on the addition of salts. [Display omitted] •Poly (phenylacetylene)s containing multiple carbohydrates with serinol spacers•Helical structures revealed by circular dichroic spectroscopy analysis•Salt-induced conformational change of the glycosylated poly (phenylacetylene)s
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	0008-6215 1873-426X
DOI:	10.1016/j.carres.2019.06.002